118908-03-5

Basic information

• Product Name: 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide
• Synonyms: 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide
• CAS NO: 118908-03-5
• Molecular Weight: 343.339
• Mol File: 118908-03-5.mol

Chemical Properties

• CAS DataBase Reference: 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide(118908-03-5)
• EPA Substance Registry System: 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide(118908-03-5)

Safety Data

• Hazardous Substances Data: 118908-03-5(Hazardous Substances Data)

Upstream product

• 23274-21-7 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole 
• 536-74-3 phenylacetylene 
• 118744-90-4 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carboxamide 
• 118907-97-4 5-(phenylethyn-1-yl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 

Downstream Products

• 147212-76-8 5-(phenylethyn-1-yl)-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide 

Relevant articles and documents

Imidazole derivatives, process for production thereof, and use thereof

Disclosed are imidazole derivatives represented by formula [I]: STR1 wherein R is a hydrogen atom or STR2 wherein R2 is a hydrogen atom or a hydroxy protecting group, R2 protecting either a single hydroxy or two hydroxies together when R2 is a hydroxy protecting group, and R3 is a hydrogen atom or OR2 ; A is CONH2 or CN; and R1 is a hydrogen atom, lower alkyl, hydroxy lower alkyl, or phenyl. Also disclosed are six processes for producing these novel compounds among which a typical process comprises reacting a starting imidazole compound having a halogen at the 5-position thereof with an acetylene derivative to alkynylate the 5-position. Furthermore, the compounds having remarkable antitumor activities and therefore can provide novel antitumor agents.

Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives

The palladium-catalyzed cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carboxamide (8) with various terminal alkynes in the presence of bis(benzonitrile)palladium dichloride in acetonitrile containing triethylamine gave the desired 5-alkynyl derivatives 9 in high yields. However, when (trimethylsilyl)acetylene was used, the only isolable product was the undesired dimer, 1,2-bis(4-carbamoyl-1-β-D-ribofuranosylimidazol-5-yl)acetylene derivative 10a. To circumvent such dimer formation, the reaction was done with use of trimethyl[(tributylstannyl)ethynyl]silane in the absence of triethylamine to afford the desired 5-(2-trimethylsilyl)ethynyl derivative 9a in good yield. Furthermore, the similar cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carbonitrile (12) with (trimethylsilyl)acetylene also afforded the desired nucleoside 13a. Deprotection of these compounds furnished 5-alkynyl-1-β-D-ribofuranosylimidazole-4-carboxamides (6b-k) and -carbonitriles (14b-f). Among these, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (6b, EICAR) is the most potent inhibitor of growth of the various tumor cells in culture including human solid tumor cells. Preliminary results of in vivo antitumor activity against murine leukemias L1210 and P388 are also described.